


Game Night

by Fallenangelcas98



Category: Supernatural
Genre: Attempt at Humor, Awkward Sexual Situations, Drinking Games, Drunk Castiel (Supernatural), Drunk Dean Winchester, Drunk Sex, Drunk flirting, Embarrassment, Fanart, First Kiss, First Time, Frottage, Handcuffed Together, Hangover, Humor, Hungover Castiel (Supernatural), Hungover Dean Winchester, M/M, Memory Loss, Third Wheel Sam Winchester, Truth or Dare
Language: English
Status: Completed
Published: 2019-12-19
Updated: 2019-12-19
Packaged: 2021-02-25 21:02:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,317
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21861892
Author URL: https://archiveofourown.org/users/Fallenangelcas98/pseuds/Fallenangelcas98
Summary: Dean and Cas wake up in bed together after a night of drinking, with no memory of what happened. Sam fills them in.
Relationships: Castiel/Dean Winchester
Comments: 2
Kudos: 180





	Game Night

**Author's Note:**

> This is set in season 9 where Cas is living in the bunker and everything is good

Dean woke up to a killer headache and overly dry mouth, groaning a little as he rubbed a hand over his face. He stopped when he realized there was a weight on his chest, looking down to see Cas lying on him, curled up close. “Oh fuck.” He murmured, trying to remember how the hell that happened. They were all drinking last night, he knew that much, but the rest is too much of a haze. He couldn’t remember anything. Certainly not _this_.

After a moment of shocked contemplation Dean tried to sit up a bit while not disturbing the ex angel, starting to regret how much he had to drink with the size of this hangover. Despite his carefulness Castiel started to stir awake, making a sound of discontentment and pulling away from Dean a little. His own eyes went wide when they opened to see the shirtless hunter by his side in the bed.

“D-Dean? What are you—w-why are we—?” He stuttered, struggling with the fact that he was in _Dean's_ room in _Dean's_ bed and that they were both—wait. They were both _naked_. He'd been pressed up against Dean Winchester’s naked body. He flushed when he realized that, putting some proper distance between them as he sat up and pulled the sheets closer to his body.

“Dean, what happened last night?” He asked, not remembering anything either. All he knew right now was that he'd woken up with a huge hangover in his best friend’s bed, _naked_ , with no recollection of how he got there. Dean gave no good answer either, replying, “I don’t know, man. I’m just as freaked as you are!”

The hunter took a deep breath, trying to compose himself. “Look, alright, lets just get dressed, go grab a coffee and some damn painkillers and try to figure this out together. And then maybe forget this ever happened and never speak of it again.” He proposed, running a hand through his hair before moving to swing his legs over the edge of the bed and get up. Before he could though, he realized there was a weight around his wrist, looking down to see fucking _handcuffs_ chaining his right hand to Cas' left. “What the hell? Why—? What the hell!” He exclaimed, meeting Cas' confused expression with his now pissed off one.

“Well, that makes things harder.” Cas stated dryly, pissing Dean off more. “You think?” He replied in annoyance, giving his wrist a slight yank and groaning again. “lets get some pants on and find the damn keys.” He said, silently asking Cas to come his way with a head nod and waiting for him to scoot closer before he tried to stand again.

They had to take turns getting their underwear on, Dean picking out some sweats and Cas picking up the jeans he’d worn the night before. They both awkwardly gave each other a bit of privacy, looking away and trying not to let curiosity take hold of them as they each covered their modesty. They had to quite embarrassedly get cleaned up too, what with the dried come on their stomachs and chests making it very clear what they did with each other. Not that it wasn’t already pretty obvious. Either way they tried to ignore the facts and just get through the awkward encounter, searching around for the keys to the handcuffs. Once they were found Dean gladly took them off, rubbing his wrist a little before getting a shirt on. “Come on, lets head to the kitchen.” Dean grumbled once Cas got a shirt on too, leaving the room with him.

* * *

16 hours ago

“Alright! Beer run is complete and we have everything we need to get this party started!” Dean exclaimed as he walked down the stairs with bags in tow. Sam and Cas were sitting on the couch in front of the tv they’d set up a while back. Dean passed them each a beer, unpacking everything else he’d bought at the same time. “I also got us some vodka shots and other assorted drinks, and snacks of course.” He explained happily, plopping down beside Cas with a smile.

“So, this’ll be your first proper time getting hammered as a human. Excited?” Dean asked Cas, taking a swig of beer.

“I don’t plan on getting that drunk, but yes, I suppose so.” He replied, taking a small sip himself.

“Come on, man, it's game night! Get in the partying spirit!” Dean encouraged, nudging his arm playfully. Cas had been without his grace and wings for a few months now, slowly getting used to the trials of being human. With some help, of course. Dean especially had been more then happy to help the poor guy, there was a lot of stuff to get used to.

Sam chuckled a little, giving Cas a sympathetic smile. “Don't worry, it’ll be fun. I'll make sure he doesn’t go too crazy.” He said, looking at Dean pointedly. The elder hunter scoffed, taking another swig. “Whatever, grandma. It’s gonna be an awesome night.”

* * *

Dean and Cas walked into the kitchen with their heads down low, heading for the coffee machine first. Sam was already there reading a newspaper, smiling far too brightly when he saw the pair enter. “Hey guys, how'd you sleep?” He asked with a knowing expression, taking a sip of his coffee.

“Just peachy.” Dean grumbled, taking a couple painkillers with Cas.

“So, last night, huh? Pretty fun.” Sam remarked, earning an annoyed scowl from both Cas and Dean. “What’s up with you? How come you’re not hungover?” Dean asked, sitting down at the table with his friend.

“Oh, I didn’t drink nearly as much as you guys did. Wait, you do remember how last night went, don’t you?” Sam asked, smiling wider when the looks each of them gave showed the answer to that question. “Oh my god, you don’t remember!” He chuckled, before getting an annoyed punch on the arm.

“No, we don’t. Care to enlighten us?” Dean asked with a scowl, finally getting his younger brother to stop with the teasing.

“Alright, alright, I’ll tell you what happened. It’s pretty embarrassing though.” He smiled, taking a sip of coffee. Castiel was more worried then Dean, given how it was his first time drinking that much as a human. He wasn’t sure what kind of drunk he was, he hoped he didn’t do anything too embarrassing.

Dean just hoped his and Cas' friendship wouldn’t be ruined after whatever happened last night. He hoped he didn’t spill his feeling in his drunken state. The feelings he kept bottled up deep down for fear of rejection.

Whatever his thoughts, last night was about to be explained to them and they should hopefully start to remember.

Sam started with the vodka shots.

* * *

13 hours ago

Cas sat back after his turn taking the shots, giggling a little and smiling triumphantly. He was two beers and 10 shots in and was already wasted. Sam had been taking it slow and Dean was trying his hardest to catch up to Cas' level of drunkenness. He needed much more with his high tolerance, but he had started feeling it after a while. They'd played a few normal games and a few drinking games, and now they were at the point where they were nicely tipsy.

“Heyy, good job buddy!” Dean praised, patting Cas on the shoulder. It hasn’t taken long for them to start sitting closer and closer, taking everything opportunity for physically contact.

“Thank you, Dean. You--you've been a v'ry good teacher.” Cas slurred with a happy smile. “And might I say, you have v'ry pretty eyes too. V'ry beau'iful.” He added flirtatiously, staring at him for the tenth time that night. Dean blushed a little, smiling back. “Oh, thank you. You’re pretty too.” He replied, staring back with his flushed, beautifully freckled face.

Sam cleared his throat for the sixth time that night after a few seconds of silence, getting Dean's attention.

“Alright, new game! Truth or dare.” Exclaimed the elder hunter, taking another shot and pointing at Sam. “You pick first, Sammy.”

Sam snorted a little, humouring him for now. “Okay. Dean, truth or dare?”

“Dare!”

“Alright, hotshot, I dare you to sing along to a song of my choosing.” He smirked, already getting his phone out to choose one.

“Pshh, easy. I have an amazing singing voice.” Dean replied confidently, waiting until he heard ‘Shake It Off' by Taylor Swift Start playing. He shrugged a little, owning it completely. It got some chuckles out of Sam and Cas, but he stuck with it until the end.

“Ha, nailed it. Cas, truth or dare?” Dean asked afterwards, taking another shot.

“Mhm, truth.”

“Since becoming human, have you jerked off yet?”

“Dude!” Sam objected, not really wanting the answer to that question.

“What? ‘M curious.” Dean defended, looking at Cas expectantly.

The ex-angel blushed, licking his lips a little before answering. “Yes. I have.”

“Dude, really? What about masturba’ing bein' a sin and all?”

Cas shrugged a little, still blushing. “’M human now. I wanted to ‘mbrace all aspects of it.”

“Well, good on you! ‘S fun, right?”

“Alright, that’s enough of that. Cas?” Sam interrupted, giving his friend a nod.

“O-Oh, okay. Sam, truth or dare?”

“Dare.”

“Okay, umm, I dare you to...” He started, trying to think of something for a moment. “Take five shots?”

Sam smiled and nodded, pouring five out as Dean made a small sound of discontent. “Nice try, bud. Next time though, give ‘im somethin' harder.”

Sam downed the shots easily, looking at Cas this time. “Cas, true or dare?”

“Dare.” He replied this time, trying to look confident as Dean has been.

“Alright, I dare you to...kiss Dean.” He proposed playfully.

Cas blushed at that, feeling butterflies form in his stomach. “O-Oh, okay. I can...do that.” He replied, turning to the guy he’d been in love with the past six or so years to kiss him on the lips, something he'd fantasised about many times. Dean looked just as nervous as Cas felt, and yet just as eager. He was trying not to show it though, giving Sam a scowl before he looked back at Cas.

Cas made the first move since it was his dare, cautiously pressing his lips against Dean's. He intended to just make it last a second, just a quick peck so he didn’t overstep any boundaries, but when Dean didn’t pull away he kept going. He was amazed and delighted that the hunter seemed to actually be _enjoying_ it, taking the opportunity to kiss him just a little harder. When he heard a tiny moan of surprise come from the hunter he felt all kinds of different emotions run though him. Giddiness, excitement, a tiny hint of arousal...

When they did eventually pull away it was only by a few inches, looking at each other with the same kind of conflicted, surprised and confused expressions. They both wanted to keep going, only hesitating a bit in their drunken states. They each had small, nagging worries in the back of their heads about the implications of crossing this line, but right now who cared? It felt so good. They each closed the distance between them, both much more eager this time. They found themselves sitting closer and cautiously touching more, feeling as though there were sparks of electricity passing between them. Dean cupped Cas' cheek gently and Cas slid a hand around Dean's waist, clutching at his shirt.

Sam had only watched for about 3.4 seconds before looking away awkwardly, not exactly surprised by this result but still feeling a bit uncomfortable. And even more like a third wheel then usual. “Alright guys, well, you have fun, I’m going to bed now.” He said loud enough to get their attention, grabbing another beer to take with him.

Dean pulled away with a flushed face, licking his lips as he carried on staring at Cas. “Okay...’night Sam...” He murmured distractedly, swallowing his nerves. He distantly heard his brother say goodnight to Cas as well before hastily heading to his bedroom, leaving them alone together.

* * *

Sam sipped his coffee once he finished with his explanation, still smiling as he looked at the pair. Dean and Cas both looked a bit uncomfortable, having started to recall how they’d acted. How much they’d flirted with each other throughout the evening. How it had felt to kiss. What happened _after_ Sam had gone to bed.

“Remember now?” Sam asked with a smirk, taking another sip of coffee.

“Yes, and now you are going to never speak of it again.” Dean replied, scowling at his brother. Sam put his hands up in defence, even though he had every intention of teasing his brother about this in the future.

“I’m assuming you two have a lot to talk about so I’ll leave you to it now.” He said, taking his empty mug to the sink before leaving the pair to themselves once again. An awkward silence fell upon the kitchen, only interrupted a moment later by Dean clearing his throat.

“So, you remember last night now?” He asked, staring at his coffee.

“Yes. Do you?”

“Yeah.”

They fell silent again before Cas worked up the courage to continue. “Do you...regret it?” He asked hesitantly. Dean finally glanced at Cas, shaking his head a little.

“No. I don’t.”

Castiel let out a small sigh of relief. So Dean really did feel the same way. Does that mean they have a future together then?

“So, where do we go from here?” The ex-angel asked as he looked up at Dean.

Dean shrugged and scooted a little closer, taking a sip of his coffee. “We wing it, I guess. See where it goes.”

Cas snorted. “How romantic.”

Dean scowled a little, shoving his arm playfully. “What would you say?”

“We go on a date, perhaps? That’s what people do when they...have feelings for one another, right?”

Dean softened his gaze and smiled a little, hesitantly pressing a kiss to Cas' cheek. “That works for me.” He replied, smiling wider at the blush that started to colour Cas' cheeks.

“Good talk. Now, can we agree to forget the embarrassing parts and just remember the fun bits from last night?” Dean asked. Cas nodded in agreement, thinking about the end of the night with a deeper blush. “It's a shame we were so drunk for our first time doing...you know. That.” He added a little sadly.

Dean nodded a little sympathetically. It had been freaking great, but not exactly meaningful. It wasn’t loving, more rushed and heated. He had wanted Cas' first time to be more special.

“Well...next time'll be nicer. Slower. If you want that, that is?” Dean asked gently.

Cas smiled at the proposal. “I-I'd like that. Thank you.” Of course, he did hope for steamy nights as well as the slow love making. He wanted to experience everything with Dean. He didn’t realize how much he'd been missing all his life.

* * *

12 hours ago

“S-So, uh, that was—” Dean started, before Cas interrupted him with another eager kiss. He melted into it, moaning as he kissed him deeper. He found himself slipping a hand under Cas' shirt, feeling him shiver under his touches. “Alright, okay, we're doin' this. Come on, follow me.” Dean said eagerly once they pulled away to breathe, taking Cas' hand and dragging him towards his bedroom.

Castiel happily followed, heart pounding in excitement. It took a little longer then they would have liked given how drunk they were, but they eventually made it. Dean shut the door by pressing Cas up against it, eagerly kissing him again with a satisfied moan. Cas opened his mouth to Dean, moaning loudly at the feeling of his tongue entering it. He couldn’t get enough, couldn’t get Dean close enough. One thing he knew was that there were too many clothes in between them, so he hastily started taking off his shirt along with Dean's too.

“Fuck, I’ve wanted this for so long. I-I didn’t think you--you—” Cas interrupted him with another heated kiss.

“Stop talking. More kissing.” Castiel ordered, pressing his lips down Dean' throat as he explored his body with his hands.

“Geez, bossy much?” Dean chuckled, taking Cas' hand after a moment to drag him to the bed. They both fell down on the memory foam, grinding and writhing, kissing and touching, moaning and cursing. Everything was so hot and primal, it felt _great_.

“Hey, Cas, what if we add a lil' bit of spiciness to this?” Dean suggested after a moment, answering the ex-angel's frown of confusion by grabbing a pair of handcuffs out of his side table and dangling them in front of him.

“Oh, is this a BSD thing? I’ve heard about that.” Cas replied, making Dean chuckle a little.

“Wh--it's called BDSM, and yes. ‘S just for a bit more fun, right?”

Castiel considered it a moment before smiling and grabbing them off Dean. He clipped the cuffs around Dean’s wrist before attaching the other side to his own wrist and throwing the key across the room.

“Now what?” Cas asked, eager to continue. Dean just laughed, gently resting his forehead against Cas' shoulder.

“You idiot, you're s'pposed to clip it ‘round the bed frame, not attach us together. Well, whatever. We can work with this.” He murmured, kissing him again as he straddled his hips. He laced their fingers together next to Cas' head and rolled his hips down slow, earning a loud moan from the man beneath him.

He kept going like that for a while, relishing in the feeling of their cocks rubbing together. When he wanted more he moved his free hand down to stroke them together, feeling Cas' hand squeeze his shoulder as he sucked a dark mark on his neck. He didn’t keep a slow pace for long, too eager and aroused for that. No, he wanted it fast and messy, loving the unabashed moans of pleasure coming from Cas.

“Fuck, you’re so hot. ‘M so close already.” Dean moaned, crashing their lips together for another desperate kiss despite his breathlessness.

“M-Me too, I—what do I—”

“Just let go, come for me.” Dean said, giving their cocks a squeeze. Castiel gasped, needed no more encouragement to do just that. He threw his head back, shivering all over as he came between them, soon feeling Dean do the same.

The elder Winchester rolled over, lazily grabbing the blanket to cover them and cuddling up close to Cas as he enjoyed the afterglow of his orgasm. “Dean, that was...amazing. Sex is amazing.”

Dean hummed in agreement, smiling against Cas' neck. “Yeah, it is. ‘S awesome.” He replied quietly.

“Does this make us lovers?” Cas asked after a moment, nuzzling a little at his hair. Dean flushed at the question, not sure where they would go after this.

“I...don’t know.”

“I hope it does, ‘cause... _olani hoath ol (I love you)_.” Cas finished the sentence in Enochian, blushing a little. Dean glanced up at the ex-angel, not sure what that meant but having a pretty good idea he knew.

“’M pretty sure I feel the same way.” He replied shyly, heart fluttering at the expression Cas gave him. He nuzzled back against his neck, pressing a little kiss there before closing his eyes. “Night, Cas.”

“Goodnight, Dean.”

* * *

2 days later

Sam walked up to their couch to see Dean and Cas dozing together at the end of a movie they’d been watching, cuddled up close. The younger Winchester smiled fondly, grabbing a blanket to put over them. Cas hummed a little, nuzzling his nose against Dean's neck.

Yeah, he could get used to this. They were finally together and happy. He just needed to get noise cancelling headphones now.


End file.
